Leeb started his career playing for the Red Deer Midget Chiefs in the Alberta Midget Hockey League. He played 3 games for his hometown Red Deer Rebels as a 15-year-old, then went on to play 4 full seasons with the Rebels. He also played in the 1998-1999 WHL All-Star game.

Leeb played in Nuremberg on the same team as his older brother Greg Leeb for 4 seasons, from 2008-2012. It was the first time the brothers had ever played on the same team. Growing up they played against each other in the WHL, IHL, AHL, and the DEL leagues.

Leeb was the creator of the website [1], a hockey handicapping website with prediction picks from the world's top professional NHL handicappers.[1] He no longer owns the website.